In this special Collab Week episode of Wantrepreneur to Entrepreneur, 8 founders come together to answer one deceptively powerful question:
Think back to a flop or failure you’ve had in your business. How did it end up feeding something that worked?
This episode covers ad campaigns that flopped, teams scaled too fast, AI projects that got ahead of the technology, a contractor who never delivered, an expo full of the wrong audience, a deal lost on the two-yard line, and a lot more. Together, the answers show that the failure itself rarely matters most. What matters is what you do with it next.
For any wantrepreneur or entrepreneur still stinging from something that didn’t work, or wondering whether you’re “failing too much,” this episode is a reminder that every founder you admire has a story like yours. You’ll hear how each one turned a setback into better data, sharper focus, new skills, and a stronger business.
✨ What You’ll Take Away
In this episode, you’ll learn:
- How scaling your team before you understand your operations can almost sink your business
- Why setting expectations up front matters most when you’re selling AI
- How a failed contractor relationship can push you to build skills you never planned to learn
- Why asking the right questions saves you time and money
- What “the deal dies in maybes” means for founders still building their sales muscle
- Why saying no to the wrong opportunities makes room for the right ones
🎙️ Meet the Collab Week Contributors
Sara Reece — Workmind
Sara Reece is the CEO and Co-Founder of Workmind, where she helps organizations use practical, operations-first automation to remove friction and grow without increasing headcount at the same pace. Over the last seven years, she has designed and implemented automation for nonprofits, small businesses, franchise systems, and Fortune 500 enterprises, drawing on a career that spans journalism, television broadcasting, environmental research, and technology. Sara is the author of The Practical Path to Operational Automation and speaks regularly on practical automation, AI, leadership, and sustainable growth.
Connect with Sara:
Website: https://workmind.cloud/
Jaimz Hodge — Cart Catalyst
Jaimz Hodge is the owner of Cart Catalyst, a Missoula, Montana agency that helps Shopify brands convert more customers by removing the hidden friction in their buying experience. From the first ad click to checkout, Jaimz and his team improve both the website and the Google Ads behind it so ecommerce businesses can scale to the next level.
Connect with Jaimz:
Website: https://www.cartcatalyst.com/
Julie Silvestri — Inside Out Box
Julie Silvestri is the founder and CEO of Inside Out Box, which builds custom software and AI tools, starting with how a company’s data is designed and organized. After studying theoretical math at Harvard, Julie spent more than a decade at startups in finance and edtech, where she managed cross-national software development teams. For more than four years, Inside Out Box has served a broad range of mid-sized companies.
Connect with Julie:
Website: https://www.insideoutbox.com/
Jane Alexander — Emma Advisor
Jane Alexander is the founder and CEO of Emma Advisor, an AI platform that helps families get from high school to college with more clarity, strategy, and confidence. Homeschooled in rural Idaho, Jane went from community college to a private university and later did graduate work at Harvard, then spent more than a decade advising leaders at over 200 colleges and universities. She built Emma Advisor on the belief that opportunity shouldn’t depend on connections or expensive consultants.
Connect with Jane:
Website: https://emmaadvisor.ai/
Felix Vicknair — United Business Works
Felix Vicknair is an executive business advisor and the founder of United Business Works, based in Chattanooga, Tennessee. He provides cost optimization services that help small businesses, nonprofits, and healthcare practices reduce expenses and run leaner, both locally and across the US.
Connect with Felix:
Website: https://unitedbusinessworks.com/
Kacy Webster — Profit Quiver
Kacy Webster is a Business Transformation Strategist, Certified AI Consultant, and the founder of Profit Quiver, based in Minburn, Iowa. With more than 30 years of executive leadership in higher education, workforce development, and enterprise transformation, she helps colleges, nonprofits, and organizations adopt AI in ways their people can trust. Her framework, the 12 Domains of Human-First AI Adoption, gives leaders a structured path to transformation that starts with culture, alignment, and readiness rather than the technology itself.
Connect with Kacy:
Website: https://www.profitquiver.com/
Drew Mehta — ThinkFraction
Drew Mehta is the founder of ThinkFraction, which helps owner-operated businesses build practical AI into their everyday workflows to grow revenue, lower costs, and improve quality. After more than 20 years in corporate, much of it in product management, Drew now combines advisory, implementation, and education to fix the leaks in his clients’ back-end operations, and he’s open about learning the entrepreneurial journey as he goes.
Connect with Drew:
Website: https://thinkfraction.xyz/
Heather Waisanen — Coastal Maverick
Heather Waisanen is the founder of Coastal Maverick, a woman-owned boutique out-of-home advertising agency in Jacksonville, Florida that helps brands nationwide with strategy, media planning, buying, negotiation, and campaign execution. After being laid off from her role as a senior media planner, she launched the agency, drawing on more than a decade of experience across the client, agency, and media owner sides of the industry. Now in her fourth year in business, Heather was named a JAX Chamber Small Business Leader of the Year and is a member of the inaugural 2026 Visionaries 200 class.
Connect with Heather:
Website: https://www.coastalmaverick.com/
